2-Aminophenol → 4-(Benzo[d]oxazol-2-yl)-2-methoxyphenol

HRID 7780

Reaction equation

[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1O>C[Si](OP(=O)=O)(C)C>[O:8]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:6]1[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([O:11][CH3:12])[CH:4]=1

Participants

Conditions

Temperature: 180 °C

Procedure

4-hydroxy-3-methoxybenzoic acid (25 g, 150 mmol) and 2-amino phenol (16 g, 150 mmol) were combined in a round bottom flask. Trimethylsilyl polyphosphate (80 mL) was added. The mixture was heated at 180° C. for 30 min. The mixture was poured over ice and allowed to stir overnight. The suspension was filtered to afford 4-(1,3-benzoxazol-2-yl)-2-methoxyphenol as a pale green solid. MS (ESI) 242 (M+H).

Workup

additionThe mixture was poured over ice
filtrationThe suspension was filtered

Sources & evidence

ORD record: ord-e0ed6a9d85f54de885301c17ac0d5c45
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087601B2

Linked notes

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