Phenylacetic Acid → HCID 18355594, compound

HRID 429447Notes

Reaction equation

HRID 429447 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=O.[C:19](OC(=O)C)(=[O:21])[CH3:20].C(N(CC)CC)C.[C:33]1([CH2:39][C:40]([OH:42])=O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(OCC)(=O)C.CCOCC.O>[C:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[C:3]3[C:2](=[CH:7][CH:6]=[C:5]([O:8][CH3:9])[CH:4]=3)[O:1][C:40](=[O:42])[C:39]=2[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:13][CH:14]=1)(=[O:21])[CH3:20]

Participants

8

Reactant 4

HCID 999Phenylacetic AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 15574183(2-Hydroxy-5-methoxyphenyl)(4-hydroxyphenyl)methanone

Product 1

HCID 18355594HCID 18355594, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of (2-hydroxy-5-methoxyphenyl)-(4-hydroxyphenyl)-methanone (0.59 g, 2.42 mmol), acetic anhydride (1.15 ml, 12.1 mmol), triethylamine (0.44 ml, 3.16 mmol), and phenyl acetic acid (0.33 g, 2.42 mmol) was stirred at 135° C. for 18 h. The resulting orange coloured solution was poured into water (20 ml) and stirred for 3 h, and the resulting mixture of aqueous solution plus sticky solid was diluted with ethyl acetate (20 ml) to dissolve the solid, and the organic layer separated. The aqueous phase was further extracted with ethyl acetate (2×20 ml). The combined organic extracts were washed with water, then brine, dried over sodium sulfate and evaporated to give a yellow/orange gum. This gum was dissolved in a minimum of ether and petrol added to precipitate the title compound as an off white powder.

Workup

  1. stirringstirred for 3 h
  2. additionthe resulting mixture of aqueous solution plus sticky solid
  3. dissolutionto dissolve the solid
  4. customthe organic layer separated
  5. extractionThe aqueous phase was further extracted with ethyl acetate (2×20 ml)
  6. washThe combined organic extracts were washed with water
  7. dry with materialbrine, dried over sodium sulfate
  8. customevaporated
  9. customto give a yellow/orange gum
  10. additionadded
  11. customto precipitate the title compound as an off white powder

Sources & evidence

ORD record
ord-e5708eadb2514201a3129e3ea4aa3618
Source dataset
uspto-grants-2001_11
Patent number
US06316494B1

Reaction notes

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