Boric Acid → HCID 66673645, compound

HRID 424025Notes

Reaction equation

HRID 424025 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:23](=[O:43])[CH:24]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:31][CH:30]=2)C(OC)=O)[CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(O)(O)O>>[CH2:16]([O:15][C:13]1[CH:12]=[C:11]([C:23](=[O:43])[CH2:24][C:29]2[CH:30]=[CH:31][C:32]([O:35][CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[CH:33][CH:34]=2)[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 7628Boric AcidHCID 66674502HCID 66674502, compound

Product 1

HCID 66673645HCID 66673645, compound

Conditions

Temperature
60 °C

Procedure

34.8 g of crude methyl 3-(3,5-dibenzyloxy-phenyl)-2-(4-benzyloxyphenyl)-3-oxopropionate prepared according to Example 2 (0.0608 mol) and 7.51 g of boric acid (0.121 mol) are introduced into a 250 ml round-bottomed flask. The medium is brought to 100° C. for 1 h, 120° C. for 1 h, 140° C. for 1 h and then 150-55° C. for 5 h while distilling off light products. The mixture is cooled to 60° C. and an aqueous solution of 8.5 g of sodium hydroxide pellets dissolved in 175 ml of water is added. The mixture is then brought to reflux for 3 h and brought back to 60° C., 250 ml of toluene are added, separation by settling is carried out, the organic phase is recovered and washed with 75 ml of water and then the toluene phase is concentrated on a rotary evaporator. 19.4 g of crude 1-(3,5-dibenzyloxyphenyl)-2-(4-benzyloxyphenyl)ethanone are recovered.

Workup

  1. additionare introduced into a 250 ml round-bottomed flask
  2. distillation150-55° C. for 5 h while distilling off light products
  3. dissolutionan aqueous solution of 8.5 g of sodium hydroxide pellets dissolved in 175 ml of water
  4. additionis added
  5. temperatureto reflux for 3 h
  6. custombrought back to 60° C.
  7. addition250 ml of toluene are added
  8. customseparation
  9. customthe organic phase is recovered
  10. washwashed with 75 ml of water
  11. concentrationthe toluene phase is concentrated on a rotary evaporator
  12. custom19.4 g of crude 1-(3,5-dibenzyloxyphenyl)-2-(4-benzyloxyphenyl)ethanone are recovered

Sources & evidence

ORD record
ord-136a65c3801546a9896eac372db715ee
Source dataset
uspto-grants-2012_01
Patent number
US08101804B2

Reaction notes

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