Monobenzone → HCID 3516602, compound

HRID 2051919Notes

Reaction equation

HRID 2051919 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].Br[CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C)P(N(C)C)(N(C)C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 79040Ethyl 2-bromopropionateHCID 10942334Sodium Methoxide

Product 1

HCID 3516602HCID 3516602, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

To 20.0 g of p-(benzyloxy)phenol in 80 ml of dry hexamethylphosphoramide is added 5.4 g of sodium methoxide. The mixture is stirred 10 minutes and 18.1 g of ethyl 2-bromopropionate is added (exotherm). After 15 minutes the mixture is heated on a steam bath for 16 hours. The mixture is poured onto ice, extracted with ether, the ether extracts washed with water, dried over magnesium sulfate and concentrated in vacuo to give off-white crystals, mp 36°-44° C. Two recrystallizations from ethanol give off-white crystals, mp 46°-49° C.

Workup

  1. temperatureAfter 15 minutes the mixture is heated on a steam bath for 16 hours
  2. additionThe mixture is poured onto ice
  3. extractionextracted with ether
  4. washthe ether extracts washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give off-white crystals, mp 36°-44° C
  8. customTwo recrystallizations from ethanol
  9. customgive off-white crystals, mp 46°-49° C.

Sources & evidence

ORD record
ord-c41e54cd253d45b7961ac07006bf532d
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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